Antioxidant and glycohydrolase inhibitory behavior of curcumin-based compounds: Synthesis and evaluation of anti-diabetic properties in vitro

被引：27

作者：

Mehrabi, Maryam ^{[1
]}

Esmaeili, Sajjad ^{[2
]}

Ezati, Mohammad ^{[2
]}

Abassi, Maryam ^{[3
]}

Rasouli, Hassan ^{[2
,4
,5
]}

Nazari, Donya ^{[3
]}

Adibi, Hadi ^{[6
]}

Khodarahmi, Reza ^{[2
,7
]}

机构：

[1] Razi Univ, Fac Sci, Dept Biol, Kermanshah, Iran

[2] Kermanshah Univ Med Sci, Med Biol Res Ctr, Hlth Technol Inst, Kermanshah, Iran

[3] Kermanshah Univ Med Sci, Student Res Comm, Kermanshah, Iran

[4] Soil & Water Res Inst SWRI, Karaj, Iran

[5] Natl Inst Genet Engn & Plant Biotechnol NIGEB, Karaj, Iran

[6] Kermanshah Univ Med Sci, Pharmaceut Sci Res Ctr, Hlth Inst, Kermanshah, Iran

[7] Kermanshah Univ Med Sci, Fac Pharm, Dept Pharmacognosy & Biotechnol, Kermanshah, Iran

来源：

BIOORGANIC CHEMISTRY | 2021年 / 110卷

关键词：

Curcumin-based derivatives; Anti-diabetic; -glucosidase; -amylase; Antioxidant; ALPHA-GLUCOSIDASE INHIBITORS; OXIDATIVE STRESS; AMYLASE; DERIVATIVES; HYPERGLYCEMIA; STABILITY; EXTRACT;

D O I：

10.1016/j.bioorg.2021.104720

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Naturally occurring anti-diabetic compound curcumin can prevent diabetes complications due to antioxidant and anti-inflammatory properties as well as the attenuation of postprandial hyperglycemia. In this line, we have synthesized thirteen curcumin based derivatives (L1?L13) by multi-component reaction, characterized by IR, 1HNMR, 13C NMR, MS, elemental analysis and evaluated for possible antioxidant properties and ?-glucosidase (?-Glu) and ?-amylase (?-Amy) inhibitory potential. The curcumin-based pyrano[2,3-d]pyrimidine derivatives could inhibit ?-Glu and ?-Amy enzyme activity which showed desirable antioxidant activity. Furthermore, among the series, L5, L12, L9, L10, L8 and L11 were identified as more potent inhibitors of ?-Glu enzyme than curcumin and the compounds of L12, L4, L9, L5, L10, L8, L13, and L11 were the stronger inhibitors of the ?-Amy enzyme in vitro. Besides, among them, L12 had the lowest IC50 for the inhibition of both enzymes. Since strong inhibitors for pancreatic ?-Amy result in the progression of severe gastrointestinal side effects, the inhibitors that show the lower ?-Amy/?-Glu inhibitory ratio have attracted much attention in medicinal chemistry. Besides, considering antioxidant characteristics of synthesized compounds, the L7 derivative with the highest antioxidant activity and the lowest ??-Amy/?-Glu inhibitory? ratio could be an appropriate candidate for further study through the rational drug design to the exploration of a new class of powerful anti-diabetic drugs.

引用

页数：14

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